Donald Trump looks on as Natalie Harp places a computer playing a news report in the Oval Office on May 30, 2025. Photo by Francis Chung/Sipa USA via Reuters
President Donald Trump’s close aide, Natalie Harp, has received harsh criticism recently, from journalists who speculate she is “unwell” to commentators who speculate the notoriously philandering Trump has an inappropriate relationship with her.
“Long before Harp sprinted down the fairways of a Scottish golf course in an effort to catch up with Trump’s motorcade, I heard plenty of stories about the absurd lengths people went to for ‘the boss,’” wrote Sarah Matthews, former deputy press secretary to the White House. “Staff reportedly steamed his pants while he was still wearing them. Trump would also ask aides to take mirrors from events if he thought they made him look especially flatteringly slim. Another time, he asked aides to steal sculptures from the U.S. embassy in London.”
Matthews added, “I worked on Trump’s 2020 campaign from June 2019 through June 2020. After that, I joined the White House press shop, where I served as White House deputy press secretary up until January 6, 2021. Back then, there was no one quite like Harp inside 1600 Pennsylvania Avenue. But the office environments, bordering on a king’s court, that have allowed her to become such a critical figure with such remarkable access were already very apparent.”
The former staffer then described the White House under Trump as analogous to the reality TV show he hosted shortly before becoming president, “The Apprentice,” in which everyone had to tread carefully and behave like a sycophant in order to avoid getting fired. She also described how Trump behaved inappropriately with one young female staffer in particular, asking that she travel with him often and using a vulgar term to describe ogling her. Finally, she pointed out that Trump staffers frequently leaked negative information about each other in order to play to Trump’s ego and get rivals punished.
“The steady stream of leaks about Harp tells me some of her colleagues clearly have it out for her,” Matthews wrote. “Publicly, they’ll defend her and fling accusations of misogyny at anyone who questions her closeness to Trump. They do so because they know she controls the flow of information to him and they need her on their side. But privately, it’s obvious some of them think she’s cuckoo for Cocoa Puffs—and that’s really saying something in an administration staffed almost entirely by fellow toadies.”
She added, “Some may look at the fact that Harp has become so weirdly close to the president in such a short amount of time and assume something sexual must be going on between them. I don’t. While their relationship is deeply bizarre, I think Harp simply understands just how Trump operates. He wants emotional support blankets; he wants people who never push back; he wants to be put on a pedestal. Harp is just better at the game than anyone else . . . for now. The problem with making your career—and life—about being the boss’s favorite is that he can always change his mind.”
Matthews concluded, “Good luck, Natalie.”
In contrast to Harp’s approach to her job, a former staffer who held an analogous position under President Barack Obama recently described his position as much less bizarre.
"I know something about this particular job," Greg Greene recently explained in The New Republic. "I managed President Barack Obama’s partisan social media accounts over much of the first year of his presidency. It’s fair to say this was a more innocent age. The watchwords I took to the work were ones like safeguards and restraint, instead of poop jet and 'What if we depicted the president as Jesus Christ.' A president’s statements, I knew, could move markets even if ventriloquized by twenty- and thirtysomethings working to channel the top guy’s voice. At every point, my colleagues and I took intentional steps to guard against loose words."